With the news that an American was among those killed recently while fighting on the side of the terror group ISIS in Syria came the revelation that he was classmates and close friends with another U.S. citizen who died in battle alongside a different anti-American extremist group on a different front line five years before.

Douglas McAuthur McCain, a 33-year-old rapper, was identified by the White House Tuesday as having been killed in the bloody conflict in Syria. The Free Syrian Army, an opposition group that fights the government of President Bashar al-Assad as well as competing rebel groups, claimed on social media McCain had been fighting with the Islamic State of Iraq and Syria (ISIS), a brutal al Qaeda breakaway organization.

A public records search traced McCain’s youth back to the Twin Cities in Minnesota and to Robbinsdale Cooper High School, which is the same school attended in the same time period by Troy Kastigar. Kastigar’s image appeared in news reports around the world in 2009 after he was killed fighting with jihadist group in Somalia, this one an al Qaeda affiliate called al-Shabab.

PHOTO: Iraqi security forces hold up a flag of the the jihadist group ISIS that they captured during an operation to regain control of Dallah Abbas, 35 miles outside of Baghdad, Iraq on Jun 28, 2014.

Prior to both their fatal trips halfway across the world, McCain and Kastigar briefly shared an address after high school, records show, and news reports today said the two were close friends.

David Brom, who was principal at the high school when the young men attended, told ABC News there was “no indication whatsoever that these two students would eventually end up fighting for al-Shabab or ISIS.”

“We never would’ve guessed that,” he said, after acknowledging that he didn’t personally remember the students after 15 years. “It was a pretty normal high school. We had pretty normal kids… I can only think it was influences beyond the high school, certainly beyond our community.”

Kastigar’s mother, Julianne Boada, told the New York Daily News today she believed the pair was “sort of searching.”

“I think both of them had a really strong desire to be needed and [be] of value,” she said.

Kastigar reportedly traveled to Somalia to join al-Shabab in 2008. After he was killed in fighting, al-Shabab featured their American recruit in a martyrdom video in which Kastigar urges his fellow Americans to join him in his holy war.

“If you guys only knew how much fun we have over here – This is the real Disneyland,” a bearded Kastigar says. “Come here and join us.”

McCain posted Kastigar’s photo on his Facebook page after his death, saying he believes his friend to be in paradise.

Public records and other social media posts do not indicate McCain ever traveled to Somali, but five years after Kastigar’s death, he did follow in his friend’s doomed footsteps by joining a militant jihadi group. He appears to have traveled to Syria earlier this year after tweeting about being eager to join his brothers. He retweeted another ISIS supporter who said, “It takes a warrior to understand a warrior. Pray for ISIS.”